JPS6234759B2 - - Google Patents
Info
- Publication number
- JPS6234759B2 JPS6234759B2 JP59162761A JP16276184A JPS6234759B2 JP S6234759 B2 JPS6234759 B2 JP S6234759B2 JP 59162761 A JP59162761 A JP 59162761A JP 16276184 A JP16276184 A JP 16276184A JP S6234759 B2 JPS6234759 B2 JP S6234759B2
- Authority
- JP
- Japan
- Prior art keywords
- cymetidine
- item
- solvent
- items
- suspension
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- -1 (5-methyl-4-imidazolyl)methylthio Chemical group 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 238000010960 commercial process Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- RKGNDHKEOIXFST-UHFFFAOYSA-N 1-cyano-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCN=C(N)NC#N RKGNDHKEOIXFST-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000937413 Axia Species 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 238000005147 X-ray Weissenberg Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3906576A GB1543238A (en) | 1976-09-21 | 1976-09-21 | Polymorph of cimetidine |
| GB39065/76 | 1976-09-21 | ||
| GB2716/77 | 1977-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60185767A JPS60185767A (ja) | 1985-09-21 |
| JPS6234759B2 true JPS6234759B2 (no) | 1987-07-28 |
Family
ID=10407431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59162761A Granted JPS60185767A (ja) | 1976-09-21 | 1984-07-31 | 複素環式化合物の新規多形体 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS60185767A (no) |
| AR (1) | AR218267A1 (no) |
| BG (1) | BG28050A3 (no) |
| CS (1) | CS207482B1 (no) |
| DD (1) | DD129906A5 (no) |
| DK (1) | DK417677A (no) |
| ES (1) | ES462517A1 (no) |
| FI (1) | FI772542A (no) |
| GR (1) | GR61173B (no) |
| IT (1) | IT1086352B (no) |
| MY (1) | MY8400026A (no) |
| NL (1) | NL7710354A (no) |
| NO (1) | NO773225L (no) |
| PL (1) | PL103681B1 (no) |
| PT (1) | PT66927B (no) |
| SE (1) | SE7710518L (no) |
| ZA (1) | ZA774857B (no) |
| ZM (1) | ZM7077A1 (no) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| JPS4975574A (no) * | 1972-09-05 | 1974-07-20 | ||
| JPS5154561A (en) * | 1974-09-02 | 1976-05-13 | Smith Kline French Lab | Guanijinkagobutsunoseiho |
-
1977
- 1977-04-18 DD DD7700198451A patent/DD129906A5/xx unknown
- 1977-05-13 GR GR53452A patent/GR61173B/el unknown
- 1977-05-17 BG BG036338A patent/BG28050A3/xx unknown
- 1977-08-11 ZA ZA00774857A patent/ZA774857B/xx unknown
- 1977-08-16 PT PT66927A patent/PT66927B/pt unknown
- 1977-08-26 FI FI772542A patent/FI772542A/fi unknown
- 1977-09-08 IT IT27402/77A patent/IT1086352B/it active
- 1977-09-12 ZM ZM7770A patent/ZM7077A1/xx unknown
- 1977-09-19 AR AR269254A patent/AR218267A1/es active
- 1977-09-20 SE SE7710518A patent/SE7710518L/xx not_active Application Discontinuation
- 1977-09-20 PL PL1977200960A patent/PL103681B1/pl unknown
- 1977-09-20 NO NO773225A patent/NO773225L/no unknown
- 1977-09-21 DK DK417677A patent/DK417677A/da not_active Application Discontinuation
- 1977-09-21 CS CS611677A patent/CS207482B1/cs unknown
- 1977-09-21 ES ES462517A patent/ES462517A1/es not_active Expired
- 1977-09-21 NL NL7710354A patent/NL7710354A/xx not_active Application Discontinuation
-
1984
- 1984-07-31 JP JP59162761A patent/JPS60185767A/ja active Granted
- 1984-12-30 MY MY26/84A patent/MY8400026A/xx unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| JPS50105664A (no) * | 1971-03-09 | 1975-08-20 | ||
| JPS4975574A (no) * | 1972-09-05 | 1974-07-20 | ||
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| JPS5154561A (en) * | 1974-09-02 | 1976-05-13 | Smith Kline French Lab | Guanijinkagobutsunoseiho |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60185767A (ja) | 1985-09-21 |
| DD129906A5 (de) | 1978-02-15 |
| DK417677A (da) | 1978-03-22 |
| ZM7077A1 (en) | 1978-08-21 |
| PL103681B1 (pl) | 1979-07-31 |
| IT1086352B (it) | 1985-05-28 |
| ZA774857B (en) | 1978-06-28 |
| CS207482B1 (en) | 1981-07-31 |
| SE7710518L (sv) | 1978-03-22 |
| MY8400026A (en) | 1984-12-31 |
| ES462517A1 (es) | 1978-07-01 |
| FI772542A (no) | 1977-08-29 |
| PL200960A1 (pl) | 1978-05-22 |
| NO773225L (no) | 1978-03-22 |
| PT66927A (en) | 1977-09-01 |
| BG28050A3 (en) | 1980-02-25 |
| PT66927B (en) | 1979-03-13 |
| NL7710354A (nl) | 1978-03-23 |
| GR61173B (en) | 1978-10-03 |
| AR218267A1 (es) | 1980-05-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009280604A (ja) | Ｎ−（４−トリフルオロメチルフェニル）−５−メチルイソオキサゾール−４−カルボキサミドの結晶形態の製造方法 | |
| JPH05208943A (ja) | Ｎ−（トランス−４−イソプロピルシクロヘキシルカルボニル）−ｄ−フェニルアラニンの結晶及びその製造法 | |
| FI101296B (fi) | Menetelmä yhdisteen N-£4-£5-(syklopentyylioksikarbonyyli)amino-1-metyy li-indol-3-yylimetyyli|-3-metoksibentsoyyli|-2-metyylibentseenisulfona midi kiteisen muodon ja sitä sisältävien pellettien valmistamiseksi | |
| Gajda et al. | The role of the polymer matrix in solvent-free hot melt extrusion continuous process for mechanochemical synthesis of pharmaceutical cocrystal | |
| KR100336229B1 (ko) | 열역학적으로 안정한1-(4-카바졸릴옥시)-3-[2-(2-메톡시페녹시)에틸아미노]-2-프로판올의 개질물, 이의 제조 방법 및 이를 함유한 약학조성물 | |
| JPS6222967B2 (no) | ||
| JP7394410B2 (ja) | ニコチンアミドモノヌクレオチド共結晶を調製する方法 | |
| CN104284897A (zh) | 替卡格雷晶型及其制备方法和用途 | |
| CN106795159A (zh) | 一种周期素依赖性蛋白激酶抑制剂的结晶形式及其制备方法 | |
| CN105061420B (zh) | 一种jak抑制剂的晶型及其制备方法和应用 | |
| WO2022000265A1 (zh) | 一种阿西替尼与戊二酸共晶及其制备方法 | |
| Han et al. | Self-gelation involved in the transformation of resveratrol and piperine from a co-amorphous system into a co-crystal system | |
| JPS6234759B2 (no) | ||
| CN115417812B (zh) | 一种阿西替尼-烟酰胺共晶及其制备方法和应用 | |
| MATSUDA et al. | Physicochemical characterization of oxyphenbutazone and solid-state stability of its amorphous form under various temperature and humidity conditions | |
| MXPA06006731A (es) | Forma polimorfica de dexcetoprofeno trometamol, su preparacion y composiciones que lo contienen. | |
| Umar et al. | Multicomponent crystal of fenofibric acid-saccharin: characterization and antihyperlipidemic effectiveness | |
| IL31558A (en) | 3'-phenylspiro(imidazolidine-2,1'-phthalan)and the tautomer 2-(2-imidazolin-2-yl)benzhydrol and process for their manufacture | |
| CN104379557A (zh) | 阿戈美拉汀晶型i的制备方法 | |
| TWI770934B (zh) | 酪胺酸激酶抑制劑的一馬來酸鹽的晶型及其製備方法 | |
| CN106810490A (zh) | 一种二芳基化合物的晶型及其制备方法和应用 | |
| AU2018256993B2 (en) | Crystal form and salt of 3-(3,5-dichloro-4-hydroxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole | |
| US3337566A (en) | Beta-hydroxy bis heterocyclic aryl derivatives of acrylonitrile | |
| JPS6056996A (ja) | ２′―デオキシ―５―トリフルオロメチルウリジン誘導体及びそれを含有する抗腫瘍剤 | |
| EP3408264A1 (en) | Nilotinib dinitrate (v) and crystalline forms thereof |